I used to travel a lot for work, and now my entire life is one big trip. Driving loafers are my go-to travel shoe. They’re turning into my go-to everything shoe. They’re amazingly versatile – they may be the most versatile shoes you own. If you don’t have a pair, try some out, then try them in these settings.

1. Business Casual

Driving loafers are perfect business casual shoes. They’re more elegant than sneakers and a lot more comfortable than most dress shoes. Those in more informal industries can wear them everyday, but bankers and lawyers may need to stick to casual Fridays. If boat shoes are a little too casual for your office, try driving loafers.

My loafers have seen a lot of miles.

2. Laid Back Weddings

The attire choices of wedding attendees range widely and wildly. Those in the wedding are often (too often?) in tuxedos while Uncle Carl will show up in cargo pants and a plaid shirt even if the invite specifies black tie. Driving loafers land right in the middle, neither too fussy nor too casual – and that makes them great for weddings (minus the black tie ones). But if you’re a dancer, they’re far from ideal, so skip them. But if you self-identify as a dancer, you already know that.

3. Air and Hotel Travel

When flying, driving loafers are easy to slip off and plop on the security belt, and they’re great slipper stand-ins on the flight. Get swollen feet while flying? Give driving loafers a shot. And if your hotel’s floor is a bit crusty, well, good thing you’ve got such comfortable shoes with you to wear around the room.

4. At the Beach, Beach Bar

Don’t want to be a flip-flop guy? Want to stand out a bit from the sandal-wearing summer pack? Try driving loafers. They’re lightweight and great sockless. Go for brown or another non-black color in these situations. Black shoes are a bit formal for the beach.

Must Reads

Comment Rules: Write only what you’d say to a person’s face. Keep it civil and when you disagree, propose an alternative. Thank you for adding to the conversation.

Porter

I just picked up my first pair. The Whiskey shade of Gibson loafers from BR. I’ve already worn it flying, poolside in the evening with shorts, and to a nice dinner. They’re amazingly comfortable, but I’m astounded by how much the leather stretched. I was shoe-horning in when I bought them, but in two weeks they’re like loose slip-ons. So folk should be aware of that when buying from Banana.

I will also say that Target now carries a simple Merona pair of them as well for around $20. The material definitely isn’t leather, feels a bit rubbery actually, but he has them too and says they’re still comfortable, so if you’re not sure about the look and want to try it out for cheap, Target may be a good bet.

cjcs

Am I the only one who finds driving loafers to be hideous? I’m all for casual leather shoes, and loafers are a great look. But that big clunky head just screams, “Crocs!” to me. Like a pair of driving gloves, driving loaders serve their purpose well, but I can’t say I approve of trying to stretch them beyond their intended use.

Mike N

I have two pairs of driving loafers – a pair of AEs and a pair of Sperrys, both have stretched significantly. Something to keep in mind in general with this type of shoe I think.

Jody Nichols

Picked up a pair from the Bass Outlet for $50 – it’s like wearing a pair of clouds.

ElixirBlack

I have the J.Crew pair and I wear them *everywhere.* They are the perfect pair for just about anything. I usually wear them to wear in the car and then switch to wingtips when I hit the office.

Gioforeal

Not all driving loafers have that shape,some brands are quite sleek,like Tods and Donald J. Pliner…

just got back from a 10 day trip across the southwest. Inspired by Paul’s road trip packing list, I wore my sperry’s driving loafers EVERYWHERE. hiked the rim of the Grand Canyon in them one morning, wore them as I drove 6 hours to a friends cabin that afternoon, and wore them at a dinner party that night. they look even better now that they’re beat to hell.

Jake

Ive had over 4 pairs and. They all stretch considerably… I think its just a loafers thing

True, but he wears em with long pants and black socks, doesn’t look weird. And there are always the no-shows.

Marshall Lilly

I’m hoping to pick up a pair of driving loafers this summer at some point (not sure what kind). In any case, I’m glad to see a list like this to help me figure out how to incorporate a new part of my wardrobe!

Marshall Lilly

Use some sort of foot powder to counteract that. The smell might be bad, but if they’re going to be worn with shorts, the end result of shorts and socks will be way worse than any odor that might occur.

big_scooter

No. I don’t like the weird tread things on the back of the heel.

Harr

Joe, don’t tell me the J.crew loafers in the picture was originally dark brown like what is currently sold at Jcrew. HA! That would be something if years of use turned the brown into sand color. I kinda like the dessert-vibe color of it, more than the dark brown one.

My question is how should a loafer fits? The Jcrew website recommends to order one half size down and so, what is your usual shoe size and what size of the Jcrew loafer is yours? I’ve never been much of a fan for slip-on as it’s incredibly hard for me to find the right balance between too tight around toes that could cause hammer toes/bend toes and too loose that it would slip out and rub against heels, without the aids of laces. I usually wear my shoes half size up and slightly loose as I dislike my little toes being constricted against the shoe surface, so it makes even harder to get shoes without laces. But the idea of having it for airplane/travel temps me again. I suppose I could get loafers with laces, but then what’s the point?

Furious Styles

I want to get a pair and can budget just one–should I go with a tan/brown or a black? I want to rock them with shorts primarily instead of sneakers. What one color should I go with?

I’ve seen this type of shoe before but never this awesome looking. I’m a heavier guy (260 lbs) so my feet hate to be in anything even with the slightest heel for an extended time. These would be perfect for work.

Oluseyi

You’ll hate them.

I’m probably still about 280, and every pair of driving loafers I’ve owned (and I’ve owned several) has the same problem. The structural separation of sole contact pads that allows the shoe to flex and thus makes it pretty good for driving ends up putting multiple islands of pressure underfoot. If you wear them for any significant duration, and especially if you stand in them a lot, they’ll make you miserable.

Pity, as they’re great shoes otherwise.

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